Water → HCID 68109281, compound

HRID 2179404Notes

Reaction equation

HRID 2179404 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][C:9]3[CH2:14][CH2:13][NH:12][CH:11]([C:15](OCC)=[O:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[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][NH:12][CH:11]([CH2:15][OH:16])[C:10]=3[C:6]=2[CH:5]=[C:4]([S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 68109155HCID 68109155, compound

Product 1

HCID 68109281HCID 68109281, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of the product of step D (51 mg, 0.12 mmol) in ethanol (5 mL) was added lithium borohydride (44 mg, 2.00 mmol) at ambient temperature. After 3 h, water (2 mL) was added and the mixture was extracted with dichloromethane (3×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, filtered and the filtrate concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate to ethyl acetate) to afford (6-chloro-8-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridin-1-yl)methanol (30 mg, 64%) as a brown oil: 1H NMR (CDCl3, 400 MHz) δ 8.01-7.94 (m, 3H), 7.82 (d, J=1.6 Hz, 1H), 7.57-7.50 (m, 3H), 4.23 (dd, J=4.0, 2.0 Hz, 1H), 3.95 (dd, J=11.2, 4.0 Hz, 1H), 3.77 (dd, J=10.8, 7.8 Hz, 1H), 3.31-3.17 (m, 2H), 2.84-2.81 (m, 2H).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo
  5. customThe residue was purified by flash column chromatography (SiO2, 8:2 hexanes/ethyl acetate to ethyl acetate)

Sources & evidence

ORD record
ord-56fbb37f5fda426bb95ed98717559977
Source dataset
uspto-grants-2015_06
Patent number
US09067949B2

Reaction notes

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