Water → (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol

HRID 602756Notes

Reaction equation

HRID 602756 reaction equation
C[O:2][C:3](=O)[C:4]([S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(=[O:25])=[O:24])([CH:6]1[CH2:18][CH2:17][C:16]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=3)[N:9]([CH2:20][O:21][CH3:22])[C:8]=2[CH2:7]1)[CH3:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].O>C1COCC1>[C:26]1([S:23]([C:4]([CH:6]2[CH2:18][CH2:17][C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[C:13]([Cl:19])[CH:14]=4)[N:9]([CH2:20][O:21][CH3:22])[C:8]=3[CH2:7]2)([CH3:5])[CH2:3][OH:2])(=[O:25])=[O:24])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 67267086(RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester

Product 1

HCID 67266793(RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 402 mg (0.84 mmol) of (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2yl)-propionic acid methyl ester in 6 mL of THF, 1.0 mL (1.0 mmol, 1.2 eq) of LiAlH4 in THF was added at RT. After 30 min, the reaction mixture was poured into water and extracted with EtOAc, dried over Na2SO4, and evaporation of the solvent afforded (RS,SR)-2-benzenesulfonyl-2-(6-chloro-9-methoxymethyl-2,3,4,9-tetrahydro-1H-carbazol-2-yl)-propan-1-ol as a colorless oil, MS: 465 (MNH4+). The crude material was used in the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over Na2SO4, and evaporation of the solvent

Sources & evidence

ORD record
ord-21d2237a432a47d6a46662c8a2949239
Source dataset
uspto-grants-2011_03
Patent number
US07906546B2

Reaction notes

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