Sodium borohydride → (S)-N-((3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl)-2-methylpropane-2-sulfinamide

HRID 2363442Notes

Reaction equation

HRID 2363442 reaction equation
[CH2:1]([N:8]1[CH2:12][C@H:11]2/[C:13](=[N:16]/[S@:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])/[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[CH2:12][C@H:11]2[C@@H:13]([NH:16][S@:17]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:18])[CH2:14][CH2:15][C@H:10]2[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 87063931(NE,S)-N-[(3aS,6aR)-2-benzyl-1,3,3a,5,6,6a-hexahydrocyclopenta[c]pyrrol-4-ylidene]-2-methylpropane-2-sulfinamide

Product 1

HCID 66590593(S)-N-((3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of (S,E)-N-((3aS,6aR)-2-benzylhexahydrocyclopenta[c]pyrrol-4(5H)-ylidene)-2-methylpropane-2-sulfinamide (0.940 g, 2.95 mmol) from Step A in methanol (20 mL) was cooled to −78° C. in a dry ice/acetone bath. Sodium borohydride (0.335 g, 8.85 mmol) was added, and the reaction was allowed to warm to room temperature overnight. The reaction was quenched with saturated aqueous ammonium chloride, and the mixture was diluted with water, and extracted with 3×100 mL of ethyl acetate. The extracts were dried (Na2SO4) and filtered. The solvent was removed in vacuo, and the crude material was chromatographed using a silica gel cartridge (Analogix®, Burlington, Wis., RS-40) with 5-50% acetone/hexanes to give (S)-N-((3aS,4S,6aR)-2-benzyloctahydrocyclopenta[c]pyrrol-4-yl)-2-methylpropane-2-sulfinamide: 1H NMR (300 MHz, CDCl3) δ ppm 7.37-7.11 (m, 5H), 4.85 (d, J=7.0, 1H), 3.90-3.71 (m, 2H), 3.28 (d, J=13.0, 1H), 3.09 (d, J=9.8, 1H), 2.72-2.50 (m, 2H), 2.46 (d, J=9.6, 1H), 2.32-2.12 (m, 2H), 1.82 (td, J=5.5, 12.7, 1H), 1.68-1.60 (m, J=10.6, 2H), 1.35-1.24 (m, 1H), 1.20 (s, J=5.5, 9H).

Workup

  1. temperatureto warm to room temperature overnight
  2. customThe reaction was quenched with saturated aqueous ammonium chloride
  3. additionthe mixture was diluted with water
  4. extractionextracted with 3×100 mL of ethyl acetate
  5. dry with materialThe extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvent was removed in vacuo
  8. customthe crude material was chromatographed

Sources & evidence

ORD record
ord-f9a2d7319b0048e0a579c3f6aa91a62e
Source dataset
uspto-grants-2014_04
Patent number
US08691865B2

Reaction notes

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