HCID 22730718, compound → 1,1-Dimethylethyl N-[4-hydroxy-1-[(phenylthio)methyl]butyl]carbamate

HRID 2356116Notes

Reaction equation

HRID 2356116 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:16][S:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:10][CH2:11][C:12](OC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH-](CC)CC)C.[Li+]>C1COCC1>[OH:13][CH2:12][CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:16][S:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 22730718HCID 22730718, compoundHCID 23664628Lithiumtriethylborohydride

Product 1

HCID 227307071,1-Dimethylethyl N-[4-hydroxy-1-[(phenylthio)methyl]butyl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of Example 384B (538 mg, 1.6 mmol) in THF (4 mL) at −50° C. was treated with 1M lithium triethylborohydride in THF (4 mL), stirred for 1 hour, poured into ice (˜15 g), and extracted with ethyl acetate (100 mL). The extract was washed with water (20 mL) and brine (10 mL), dried (MgSO4), filtered, and concentrated to provide the desired product of sufficient purity for subsequent use.

Workup

  1. extractionextracted with ethyl acetate (100 mL)
  2. washThe extract was washed with water (20 mL) and brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8378bf771a6f4d2998c1b76f01d480e3
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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