Ethyl Acetate → HCID 19985738, compound

HRID 974330Notes

Reaction equation

[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([C:12]([CH:14]3[CH2:16][CH:15]3[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=O)[CH2:8][CH2:9][C:10]=2[N:11]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[Cl-].[NH4+]>O1CCCC1>[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:12][CH:14]3[CH2:16][CH:15]3[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:8][CH2:9][C:10]=2[N:11]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of 2.0 g (6.4 mmol) of 2-amino-6-(2-phenyl-1-cyclopropyl-carbonyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine (melting point: 122°-126° C.; prepared from 2-phenyl-1-cyclopropyl-carboxylic acid chloride and 2 equivalents of 2-amino-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine in chloroform) in 40 ml of tetrahydrofuran is added dropwise, with stirring and under nitrogen, to 0.73 g (19.1 mmol) of lithium aluminium hydride in 40 ml of tetrahydrofuran. The mixture is stirred for 2 hours in a bath at 40° C., then cooled, ethyl acetate is added to decompose any excess lithium aluminium hydride and hydrolysis is carried out by dropwise addition of saturated ammonium chloride solution. The precipitate is filtered off and the filtrate is evaporated down in vacuo. The evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=10:1). Yield: 0.65 g (34% of theory), Melting point: 109°-113° C. (isopropanol).

Workup

temperaturecooled
filtrationThe precipitate is filtered off
customthe filtrate is evaporated down in vacuo
customThe evaporation residue is purified by column chromatography on silica gel (chloroform/methanol=10:1)

Sources & evidence

ORD record: ord-81b2db35bb324a70954816522d627dc2
Source dataset: uspto-grants-1991_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05068325

Reaction notes

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