Aluminium lithium hydride → HCID 86584831, compound

HRID 458308Notes

Reaction equation

HRID 458308 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:23](=[O:28])N(OC)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[CH:23]=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86584830HCID 86584830, compound

Product 1

HCID 86584831HCID 86584831, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 1.5 g (3.5 mmol) (2S,4R)-4-(4-methoxy-benzylsulfanyl)-2-(methoxy-methyl-carbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester dissolved in 15 ml was added to 4.2 ml (4.2 mmol, 1M THF solution) of LAH in 50 ml THF at −78° C. The reaction was was warmed up to −30° C., cooled to −78° C. and quenched with a suspension of 1.2 g silica gel/1.2 g MgSO47H2O in 5 ml aqueous 10% KHSO4. The suspension was stirred for 15 min at room temperature, filtered and washed with THF. After evaporation of the THF, the residue was taken up in CH2Cl2, dried over Na2SO4 and evaporated to give 1.2 g (98%) of (2S,4R)-2-formyl-4-(4-methoxy-benzylsulfanyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, MS: 351 (M+).

Workup

  1. temperaturecooled to −78° C.
  2. customquenched with a suspension of 1.2 g silica gel/1.2 g MgSO47H2O in 5 ml aqueous 10% KHSO4
  3. filtrationfiltered
  4. washwashed with THF
  5. customAfter evaporation of the THF
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-4f48b39b81254ee8b73b790f51f6cb7c
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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