Methanol → HCID 68310772, compound

HRID 633848Notes

Reaction equation

HRID 633848 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][O:13][C@H: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])[O:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 68311093HCID 68311093, compound

Product 1

HCID 68310772HCID 68310772, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of borane dimethyl sulphide complex in tetrahydrofuran (2.0 M, 289 μL, 0.58 mmol, 3.0 eq) is added dropwise at 0° C. to a stirred solution of (2S,5R)-(5-tert-butoxycarbonylamino-tetrahydro-pyran-2-yl)-acetic acid (50 mg, 0.19 mmol, 1.0 eq) in tetrahydrofuran (2 mL). The reaction mixture is stirred at 0° C. for 30 minutes then at room temperature for 2 hours. Methanol (2 mL) is cautiously added to the reaction mixture that is then evaporated, repeatedly treated with methanol and concentrated to dryness to afford (3R,6S)-[6-(2-hydroxy-ethyl)-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester as a white solid (47 mg, 99% yield).

Workup

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

Sources & evidence

ORD record
ord-8c6ae007f75b4d25a941db1936ae9414
Source dataset
uspto-grants-2016_04
Patent number
US09321788B2

Reaction notes

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