Hydrochloric Acid → HCID 22671560, compound

HRID 1006853Notes

Reaction equation

HRID 1006853 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([O:14][CH2:15][CH:16]1[CH2:20][N:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:18][CH:17]1[CH2:25][S:26]C(=O)C)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.Cl>CCOCC>[CH2:7]([O:14][CH2:15][CH:16]1[CH2:20][N:19]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:18][CH:17]1[CH2:25][SH:26])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 86584858HCID 86584858, compound

Product 1

HCID 22671560HCID 22671560, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of LiAlH4 (0.23 mmol, 1 M in THF) in Et2O (6 ml) was added a suspension of thioacetic acid (3RS,4RS)—S-(4-benzyloxymethyl-1-methanesulfonyl-pyrrolidin-3-ylmethyl) ester (75.5 mg, 0.21 mmol) in Et2O. The mixture was stirred at RT for 30 min and refluxed for 2 h. After cooling to r.t., water and 1 M aqueous HCl were added. The organic phase was dried and evaporated to give 63 mg (95%) of [(3RS,4RS)-4-benzyloxymethyl-1-methanesulfonyl-pyrrolidin-3-yl]-methanethiol as a colorless oil, MS: 333 (M+NH4)+.

Workup

  1. temperaturerefluxed for 2 h
  2. temperatureAfter cooling to r.t.
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-54d93bafb50944348d3446a7382e262e
Source dataset
uspto-grants-2004_09
Patent number
US06790860B2

Reaction notes

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