Methanol → HCID 178453956, compound

HRID 1354227Notes

Reaction equation

HRID 1354227 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15](O)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO>C1COCC1>[OH:16][CH2:15][C@H:12]1[CH2:11][CH2:10][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 887MethanolHCID 178453972HCID 178453972, compound

Product 1

HCID 178453956HCID 178453956, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of borane dimethyl sulphide complex (2.85 ml, 30 mmol) in THF (50 ml) was added dropwise at 0° C. to a solution of trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (2.43 g, 10 mmol) in THF (100 ml). The reaction mixture was stirred at 0° C. for 15 minutes and at room temperature for 3 hours, methanol was cautiously added and the mixture was concentrated. The crude product was repeatedly treated with methanol and concentrated again, and finally dried under a high vacuum. Used without further purification.

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe crude product was repeatedly treated with methanol
  3. concentrationconcentrated again
  4. customfinally dried under a high vacuum
  5. customUsed without further purification

Sources & evidence

ORD record
ord-4d28b64237d94c47ab35c18f4b564d49
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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