4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester → 4-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl ester

HRID 446967Notes

Reaction equation

HRID 446967 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:9][N:8](C(OCC2C=CC=CC=2)=O)[CH:7]2[CH2:20][CH2:21][N:22]([C:23](=[O:39])[CH:24]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:6]12)=[O:4]>CO.[Pd]>[CH3:1][O:2][C:3]([CH:5]1[CH2:9][NH:8][CH:7]2[CH2:20][CH2:21][N:22]([C:23](=[O:39])[CH:24]([NH:31][C:32]([O:34][C:35]([CH3:37])([CH3:36])[CH3:38])=[O:33])[CH:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[CH:6]12)=[O:4]

Participants

4

Reactant 1

HCID 672814894-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-hexahydro-pyrrolo[3,2-b]pyrrole-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester

Product 1

HCID 672807484-(2-tert-Butoxycarbonylamino-2-cyclohexyl-acetyl)-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid methyl esterYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 16 (1.2 g, 2.2 mmol) in MeOH (30 mL) was treated with Pd/C (10% wet, 354 mg) and placed under H2 (50 psi) using a Parr apparatus. After 1.5 h, the reaction mixture was filtered through syringe filter disc (Acrodisc-PSF-0.45 μM) and rinsed with MeOH. The filtrate was concentrated to afford crude 27 (0.9 g) as a glassy solid which was used without further purification. 1H NMR (CDCl3, 300 MHz): δ5.23 (d, J=9.0 Hz, 1H), 4.83 (dd, J=2.1, 6.0 Hz, 1H), 4.32-4.21 (m, 2H), 4.03 (app t, J=9.9 Hz, 1H), 3.77 (s, 3H), 3.86-3.32 (m, 1H), 3.25-3.23 (m, 1H), 2.49-2.42 (m, 1H), 2.27-2.13 (m, 1H), 1.72-1.59 (m, 6H), 1.42 (s, 9H), 1.31-0.99 (m, 6H) ppm; 13C NMR (CDCl3, 75 MHz): δ172.1, 171.5, 156.1, 79.9, 65.4, 61.8, 56.8, 52.9, 50.2, 49.3, 46.4, 41.0, 30.4, 29.9, 28.5, 28.3, 26.2, 26.1, 26.0 ppm.

Workup

  1. filtrationthe reaction mixture was filtered through syringe
  2. filtrationfilter disc (Acrodisc-PSF-0.45 μM)
  3. washrinsed with MeOH
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-70f3891f16fe43d2a9cc651f4bf925f6
Source dataset
uspto-grants-2013_07
Patent number
US08481495B2

Reaction notes

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