4,5-Epoxy-7-nitro-2,3,4,5-tetrahydro-benzoxepin → Trans-7-nitro-5-(5-(R,S)-methyl-2-oxo-pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol

HRID 1613603Notes

Reaction equation

HRID 1613603 reaction equation
O1C2C1CCOC1C=CC([N+]([O-])=O)=CC=12.[N+:16]([C:19]1[CH:20]=[CH:21][C:22]2[O:28][CH2:27][CH2:26][C@@H:25]([O:29][Si](C)(C)C)[C@H:24]([N:34]3[CH:38]([CH3:39])[CH2:37][CH2:36][C:35]3=[O:40])[C:23]=2[CH:41]=1)([O-:18])=[O:17]>>[N+:16]([C:19]1[CH:20]=[CH:21][C:22]2[O:28][CH2:27][CH2:26][C@@H:25]([OH:29])[C@H:24]([N:34]3[CH:38]([CH3:39])[CH2:37][CH2:36][C:35]3=[O:40])[C:23]=2[CH:41]=1)([O-:18])=[O:17]

Participants

3

Reactant 2

HCID 145805224,5-Epoxy-7-nitro-2,3,4,5-tetrahydro-benzoxepinHCID 131717814trans-7-nitro-5-(5-(R,S)-methyl-2-oxo-pyrrolidin-1-yl)-4-trimethylsilyloxy-2,3,4,5-tetrahydro-1-benzoxepin

Product 1

HCID 131717813Trans-7-nitro-5-(5-(R,S)-methyl-2-oxo-pyrrolidin-1-yl)-2,3,4,5-tetrahydro-1-benzoxepin-4-ol

Procedure

Starting from 10.4 g (50 mmol) of 4,5-epoxy-7-nitro-2,3,4,5-tetrahydro-1-benzoxepin, 6.7 g of trans-7-nitro-5-(5-(R,S)-methyl-2-oxo-pyrrolidin-1-yl)-4-trimethylsilyloxy-2,3,4,5-tetrahydro-1-benzoxepin melting in the range 179°-185° C. are isolated. After elimination of the silyl group and after crystallization and chromatography on silica gel (ethyl acetate/cyclohexane 7:3) the diastereomers A and B are obtained.

Workup

  1. customare isolated
  2. customAfter elimination of the silyl group and after crystallization and chromatography on silica gel (ethyl acetate/cyclohexane 7:3) the diastereomers A and B
  3. customare obtained

Sources & evidence

ORD record
ord-cfd711e206c54fc38049f67a18544328
Source dataset
uspto-grants-1993_03
Patent number
US05194442

Reaction notes

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