Methanol → HCID 178453925, compound

HRID 1422693Notes

Reaction equation

HRID 1422693 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][C:16](O)=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][CH2:16][OH:17])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 112538972-((1s,4s)-4-(((Tert-butoxy)carbonyl)amino)cyclohexyl)acetic acid

Product 1

HCID 178453925HCID 178453925, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-5 °C

Procedure

A solution of borane dimethyl sulphide complex in tetrahydrofuran (11.7 mL, 23.32 mmol, 3.0 eq) is added dropwise within 10 minutes at −5° C. to a stirred solution of (4-tert-butoxycarbonylamino-cyclohexyl)-acetic acid (2.0 g, 7.77 mmol, 1.0 eq) in tetrahydrofuran (50 mL). The reaction mixture is stirred at −5° C. for 20 minutes then at room temperature for 3 hours. Methanol (10 mL) is cautiously added to the reaction mixture that is then evaporated and repeatedly treated with methanol and concentrated to dryness to afford [trans-4-(2-hydroxy-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester as a white solid (1.89 g, 99.5% yield).

Workup

  1. waitat room temperature for 3 hours
  2. customis then evaporated
  3. additionrepeatedly treated with methanol
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-2a40cf12f3094c26b3b5ff5d08c7e952
Source dataset
uspto-grants-2015_01
Patent number
US08927542B2

Reaction notes

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