Sodium borohydride → 2-Benzyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalen-7-ol

HRID 1013420Notes

Reaction equation

HRID 1013420 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:17][CH:16]2[CH:12]([C:13](=[O:21])[C:14]3[CH:20]=[CH:19][S:18][C:15]=32)[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[CH2:17][CH:16]2[CH:12]([CH:13]([OH:21])[C:14]3[CH:20]=[CH:19][S:18][C:15]=32)[CH2:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 1317290322-Benzyl-2,3,3a,7a-tetrahydro-1H-4-thia-2-aza-cyclopenta[alpha]pentalen-7-one

Product 1

HCID 1317270502-Benzyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalen-7-ol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (1664 mg, 44 mmol) was added in portions to a solution of the product of step e) (1183 mg, 4.40 mmol) in methanol at 0° C. The reaction mixture was allowed to come to room temperature and was stirred overnight. The solvent was evaporated and the residue was diluted with brine (50 ml) and extracted with ethyl acetate (2×50 mL). The combined organic extracts were dried with MgSO4 and solvent evaporated in vacuo to afford the subtitle compound (1192 mg, quantitative conversion) that was used without further purification. MS calculated for C16H17NOS +H: 272, observed: 272.

Workup

  1. customto come to room temperature
  2. customThe solvent was evaporated
  3. additionthe residue was diluted with brine (50 ml)
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. dry with materialThe combined organic extracts were dried with MgSO4 and solvent
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-f5239b0e74da496f877b5a3ed83421d3
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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