Benzyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)-propyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate → tert-Butyl (1S)-2-(4-cyanophenoxy)-1-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylmethyl)ethylcarbamate

HRID 857176Notes

Reaction equation

HRID 857176 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:29][O:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=1)[CH2:10][N:11]1[CH2:15][CH:14]2[CH2:16][N:17](C(OCC3C=CC=CC=3)=O)[CH2:18][CH:13]2[CH2:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:37]([C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:29][C@@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:10][N:11]2[CH2:12][CH:13]3[CH:14]([CH2:16][NH:17][CH2:18]3)[CH2:15]2)=[CH:36][CH:35]=1)#[N:38]

Participants

4

Reactant 1

HCID 69662314Benzyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)-propyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate

Product 1

HCID 86591446tert-Butyl (1S)-2-(4-cyanophenoxy)-1-(hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylmethyl)ethylcarbamateYield 63.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

Benzyl 5-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-cyanophenoxy)-propyl]hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (3.6 g, 6.9 mmol; from step (i) above) was dissolved in ethanol (300 mL of 95%) and hydrogenated over 5% Pd/C (w/w). The reaction was stopped when the theoretical amount of H2 (173 mL) was consumed. The mixture was filtered (through Celite®) and then evaporated. Purification by chromatography on silica (DCM, 5% MeOH eluant) gave 1.7 g (63.6%) of the title compound.

Workup

  1. customwas consumed
  2. filtrationThe mixture was filtered (through Celite®)
  3. customevaporated
  4. customPurification by chromatography on silica (DCM, 5% MeOH eluant)

Sources & evidence

ORD record
ord-010f011592e14a28a821964215497b24
Source dataset
uspto-grants-2006_12
Patent number
US07144914B2

Reaction notes

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