Acetic Anhydride → (3aR*,10aS*)-4-Acetyl-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

HRID 356160

Reaction equation

HRID 356160 reaction equation
[CH2:1]([N:8]1[C:14](=[O:15])[C@H:13]2[CH2:16][CH2:17][CH2:18][C@H:12]2[NH:11][C:10]2[CH:19]=[CH:20][CH:21]=[CH:22][C:9]1=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23](OC(=O)C)(=[O:25])[CH3:24]>>[C:23]([N:11]1[C@@H:12]2[CH2:18][CH2:17][CH2:16][C@@H:13]2[C:14](=[O:15])[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]2[CH:22]=[CH:21][CH:20]=[CH:19][C:10]1=2)(=[O:25])[CH3:24]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 70109795(3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta [e][1,4]diazepin-10(1H)-one

Product 1

HCID 70110285(3aR*,10aS*)-4-Acetyl-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-oneYield 77%

Conditions

Temperature
100 °C

Procedure

A mixture of (3aR*,10aS*)-9-benzyl-2,3,3a,4,9,10a-hexahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (1.47 g, 5.0 mmol) and acetic anhydride (5 mL) was stirred for 35 minutes at 100° C. Resulting crystalline precipitate was collected by filtration, which was washed with ethanol to give 1.29 g (yield 77%) of the titled compound, m.p. 209°-210° C.

Workup

  1. filtrationResulting crystalline precipitate was collected by filtration, which
  2. washwas washed with ethanol

Sources & evidence

ORD record
ord-964ef6054fd64222a4d6a736aaf7519d
Source dataset
uspto-grants-1998_11
Patent number
US05834463

Linked notes

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