Practical synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis

Chemistry

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https://doi.org/10.1055/s-2006-939036
Final published version

Keywords

ACID, ORGANOCATALYSIS, ASYMMETRIC MANNICH, PROLINE, ROUTE, flow, hydrogenation, organocatalysis, 5-PYRROLIDIN-2-YLTETRAZOLE, INCREASED REACTIVITY, tetrazole, ALDOL REACTIONS, asymmetric, synthesis

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Practical synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis. / Franckevicius, Vilius; Knudsen, KR; Ladlow, M et al.
In: SYNLETT, Vol. 2006, No. 6, 04.04.2006, p. 889-892.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Bibtex

@article{3ca5d624cc0b41b990ef984f525276d6,

title = "Practical synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis",

abstract = "A practical, safe, high-yielding and efficient synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole has been developed, which avoids the generation of ammonium azide in the cyclisation step and the use of a 9:1 acetic acid-water mixture as the solvent in the hydrogenation. The previously extended hydrogenolysis reaction time (three days) is now reduced to hours through the use of an H-Cube (TM) (a continuous-flow reactor employing a mixed hydrogen-liquid flow stream).",

keywords = "ACID, ORGANOCATALYSIS, ASYMMETRIC MANNICH, PROLINE, ROUTE, flow, hydrogenation, organocatalysis, 5-PYRROLIDIN-2-YLTETRAZOLE, INCREASED REACTIVITY, tetrazole, ALDOL REACTIONS, asymmetric, synthesis",

author = "Vilius Franckevicius and KR Knudsen and M Ladlow and DA Longbottom and SV Ley",

year = "2006",

month = apr,

day = "4",

doi = "10.1055/s-2006-939036",

language = "English",

volume = "2006",

pages = "889--892",

journal = "SYNLETT",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

number = "6",

}

RIS

TY - JOUR

T1 - Practical synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole, incorporating efficient protecting group removal by flow-reactor hydrogenolysis

AU - Franckevicius, Vilius

AU - Knudsen, KR

AU - Ladlow, M

AU - Longbottom, DA

AU - Ley, SV

PY - 2006/4/4

Y1 - 2006/4/4

N2 - A practical, safe, high-yielding and efficient synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole has been developed, which avoids the generation of ammonium azide in the cyclisation step and the use of a 9:1 acetic acid-water mixture as the solvent in the hydrogenation. The previously extended hydrogenolysis reaction time (three days) is now reduced to hours through the use of an H-Cube (TM) (a continuous-flow reactor employing a mixed hydrogen-liquid flow stream).

AB - A practical, safe, high-yielding and efficient synthesis of (S)-pyrrolidin-2-yl-1H-tetrazole has been developed, which avoids the generation of ammonium azide in the cyclisation step and the use of a 9:1 acetic acid-water mixture as the solvent in the hydrogenation. The previously extended hydrogenolysis reaction time (three days) is now reduced to hours through the use of an H-Cube (TM) (a continuous-flow reactor employing a mixed hydrogen-liquid flow stream).

KW - ACID

KW - ORGANOCATALYSIS

KW - ASYMMETRIC MANNICH

KW - PROLINE

KW - ROUTE

KW - flow

KW - hydrogenation

KW - organocatalysis

KW - 5-PYRROLIDIN-2-YLTETRAZOLE

KW - INCREASED REACTIVITY

KW - tetrazole

KW - ALDOL REACTIONS

KW - asymmetric

KW - synthesis

U2 - 10.1055/s-2006-939036

DO - 10.1055/s-2006-939036

M3 - Journal article

VL - 2006

SP - 889

EP - 892

JO - SYNLETT

JF - SYNLETT

SN - 0936-5214

IS - 6

ER -

Research

Text available via DOI:

Keywords