(S)-N-[2-(4-chlorophenyl)-2-cyclopropylacetyl]-4-(1-methylethyl)-2-oxazolidinone → 2-Cyclopropyl-2-(4-chlorophenyl)ethanol

HRID 1383224Notes

Reaction equation

HRID 1383224 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH:20]2[CH2:22][CH2:21]2)[C:9](N2[C@@H](C(C)C)COC2=O)=[O:10])=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH:20]1([CH:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[CH2:9][OH:10])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 15616710(S)-N-[2-(4-chlorophenyl)-2-cyclopropylacetyl]-4-(1-methylethyl)-2-oxazolidinone2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 156167072-Cyclopropyl-2-(4-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This compound was prepared in a manner analogous to that of Step F, using 0.80 gram (0.0025 mole) of diastereomer (B) of (S)-N-[2-(4-chlorophenyl)-2-cyclopropylacetyl]-4-(1-methylethyl)-2-oxazolidinone (prepared in Example 3, Step E) and 0.30 gram (0.008 mole) of lithium aluminum hydride in 15 mL of tetrahydrofuran. The yield of stereoisomer (B) of 2-cyclopropyl-2-(4-chlorophenyl)ethanol was 0.45 gram as an oil.

Workup

  1. customThis compound was prepared in a manner analogous to that of Step F

Sources & evidence

ORD record
ord-fbb79b82fa264e85bbc7a2d8a721dc70
Source dataset
uspto-grants-1989_02
Patent number
US04808762

Reaction notes

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