Sodium borohydride → HCID 54765766, compound

HRID 1503289Notes

Reaction equation

HRID 1503289 reaction equation
C(OC1[O:5][CH:6]=[C:7]([C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]([C:18]3[CH:36]=[CH:35][C:21]([O:22][C:23]4[CH:24]=[CH:25][C:26]([C:31]([F:34])([F:33])[F:32])=[C:27]([CH:30]=4)[C:28]#[N:29])=[CH:20][CH:19]=3)[CH:10]=2)N=1)C.[BH4-].[Na+].CC[OH:41].C1COCC1>>[OH:41][CH:7]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([C:18]2[CH:19]=[CH:20][C:21]([O:22][C:23]3[CH:24]=[CH:25][C:26]([C:31]([F:34])([F:33])[F:32])=[C:27]([CH:30]=3)[C:28]#[N:29])=[CH:35][CH:36]=2)[CH:10]=1)[CH2:6][OH:5]

Participants

4

Reactant 3

HCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 86700966HCID 86700966, compound

Product 1

HCID 54765766HCID 54765766, compoundYield 70%

Procedure

A mixture of compound 50 (0.15 g) and NaBH4 (100 mg) in 10 mL of EtOH/THF (1/1) was shaken at room temperature for 2 hours. The reaction was quenched with water, extracted with TCM and purified by column (MeOH/TCM 0.5/10, Rf 0.5) to give the title compound 51 as a white solid (90 mg, 70%): 1H-NMR (400 MHz, CD3OD) δ: 7.83 (d, 1H, 8.9 Hz), 7.76-7.78 (m, 1H), 7.6-7.63 (m, 2H), 7.57 (s, 1H), 7.54-7.56 (m, 1H), 7.49-7.5 (m, 1H), 7.39-7.42 (m, 1H), 7.15-7.3 (m, 4H), 4.68-4.71 (m, 1H), 3.97-4.02 (m, 1H), 3.8-3.84 (m, 1H); LC/MS: m/z=461.0 [M+Na+] (Calc: 438.4).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with TCM
  3. custompurified by column (MeOH/TCM 0.5/10, Rf 0.5)

Sources & evidence

ORD record
ord-bfd40c1efcf64e5b8b76a79e86c572c6
Source dataset
uspto-grants-2015_12
Patent number
US09212139B2

Reaction notes

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