Sodium borohydride → (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-(hydroxymethyl)naphthalen-2-yl)acetate

HRID 514027Notes

Reaction equation

[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH:22]=[O:23])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH2:22][OH:23])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:24]1[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-formylnaphthalen-2-yl)acetate (12 mg, 0.0283 mmol) in DCM/EtOH (1/1, 1 mL) at 0° C., was added NaBH4 (2 mg, 0.053 mmol) and the reaction mixture stirred at 0° C. for 2 h. The reaction was quenched by adding sat. NH4Cl. The resulting mixture was extracted with DCM, dried over MgSO4, filtered, concentrated in vacuo and purified by flash column chromatography (silica gel, ethyl acetate/hexanes) to provide 8 mg of the desired product. 1H-MNR 400 MHz (CDCl3) δ: 7.85 (s, 1H), 7.78 (d, J=4.0 Hz, 1H), 7.46-7.38 (m, 4H), 7.30-7.26 (m, 1H), 7.20-7.15 (m, 2H), 5.13 (s, 1H), 5.02 (d, J=6.2 Hz, 1H), 4.54 (d, J=6 Hz, 1H), 4.12-4.02 (m, 2H), 3.82 (bs, 1H), 1.14 (t, J=7 Hz, 3H), 1.01 (s, 9H).

Workup

customThe reaction was quenched
additionby adding sat. NH4Cl
extractionThe resulting mixture was extracted with DCM
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by flash column chromatography (silica gel, ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-93091df53ca5470f9d3bd29ca173b0b9
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102614B2

Reaction notes

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