Water → HCID 68109544, compound

HRID 2179417Notes

Reaction equation

HRID 2179417 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=4)[CH:11]([C:24](OCC)=[O:25])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH:3]=1.[BH4-].[Li+].O>C(O)C>[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][N:12]([CH2:15][C:16]4[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=4)[CH:11]([CH2:24][OH:25])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:29]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 68108852HCID 68108852, compound

Product 1

HCID 68109544HCID 68109544, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The product obtained from step A (269 mg, 0.50 mmol) was dissolved in ethanol (10 mL) at 0° C. Lithium borohydride (220 mg, 10.0 mmol) was added slowly and the reaction mixture was stirred at ambient temperature for 2 h. Water (10 mL) was added and the mixture was extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over MgSO4, filtered, and the filtrate concentrated in vacuo. Purification by flash column chromatography (SiO2, 9:1 to 7:3 hexanes/ethyl acetate) afforded (6-chloro-2-(4-methoxybenzyl)-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-1-yl)methanol (149 mg, 60%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 8.05-7.94 (m, 3H), 7.86-7.83 (m, 1H), 7.57-7.48 (m, 3H), 7.26-7.21 (m, 3H), 6.92-6.87 (m, 2H), 4.02-3.98 (m, 1H), 3.82 (s, 3H), 3.83-3.80 (m, 1H), 3.72 (s, 2H), 3.64-3.57 (m, 1H), 3.29-3.19 (m, 1H), 3.12-2.98 (m, 2H), 2.68-2.60 (m, 1H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×20 mL)
  2. dry with materialThe combined organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customPurification by flash column chromatography (SiO2, 9:1 to 7:3 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-ffeda584b3f044d4807cc970eb54627e
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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