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

HRID 1092470Notes

Reaction equation

HRID 1092470 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, 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. additiondiluted 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-5fd6f06dd9fd44b48e9c42544c28e4da
Source dataset
uspto-grants-2012_03
Patent number
US08129417B2

Reaction notes

Loading…