Sodium borohydride → HCID 86701545, compound

HRID 2173977Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of (±)-7-methyl-4-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)-1-tosyl-1H-indole-5-carbaldehyde (221 mg, 0.52 mmol) and NaBH4 (98 mg, 2.6 mmol) in EtOH (5 mL) was stirred at 0° C. for 0.5 h. The reaction mixture was diluted with CH2Cl2. The mixture was washed with H2O, half satd. KHSO4 aqueous solution, H2O, and brine, dried over Na2SO4, and then filtered. Concentration of the filtrate gave the title compound, which was used in the next reaction without any further purification. 1H NMR (400 MHz, DMSO-d6) δ 7.83 (d, J=3.79 Hz, 1H), 7.60 (d, J=8.34 Hz, 2H), 7.38 (d, J=8.34 Hz, 2H), 7.14 (s, 1H), 6.98 (d, J=3.79 Hz, 1H), 5.01 (t, J=5.56 Hz, 1H), 4.87 (d, J=11.37 Hz, 1H), 4.67 (d, J=11.37 Hz, 1H), 4.55-4.63 (m, 3H), 3.73-3.85 (m, 1H), 3.37-3.51 (m, 1H), 2.34 (s, 3H), 2.08 (s, 3H), 1.51-1.71 (m, 2H), 1.30-1.51 (m, 4H).

Workup

washThe mixture was washed with H2O, half
dry with materialKHSO4 aqueous solution, H2O, and brine, dried over Na2SO4
filtrationfiltered

Sources & evidence

ORD record: ord-175457ee0dec43ec851b39da95f6bab3
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09056874B2

Reaction notes

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