HCID 86596909, compound → HCID 86610537, compound

HRID 1455466Notes

Reaction equation

HRID 1455466 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C@H:5]([CH2:20][O:21]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:4]1>C(O)(=O)C.CC#N>[OH:21][CH2:20][C@@H:5]1[CH2:4][C@H:3]([O:2][CH3:1])[CH2:8][CH2:7][C@@H:6]1[NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 1

HCID 86596909HCID 86596909, compound

Product 1

HCID 86610537HCID 86610537, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

A sample of benzyl (1S,2R,4R)-4-methoxy-2-(trityloxymethyl)cyclohexylcarbamate (0.53 g) was dissolved in a mixture of 70% aqueous acetic acid (10 mL) and MeCN (10 mL) and stirred at 60° C. for 2 h. Reaction mixture was cooled and evaporated. Dissolved in EtOAc and washed with saturated NaHCO3 followed by brine and then dried (MgSO4). Filtered, concentrated and chromatographed to get benzyl (1S,2R,4R)-2-(hydroxyl methyl)-4-methoxycyclohexylcarbamate (0.24 g, yield=83%) as a clear oil. MS found: (M+H)+=294.29

Workup

  1. customReaction mixture
  2. temperaturewas cooled
  3. customevaporated
  4. dissolutionDissolved in EtOAc
  5. washwashed with saturated NaHCO3
  6. dry with materialdried (MgSO4)
  7. filtrationFiltered
  8. concentrationconcentrated
  9. customchromatographed

Sources & evidence

ORD record
ord-9057b76ab8de4f80aa5b26edf7cb30b8
Source dataset
uspto-grants-2009_01
Patent number
US07482335B2

Reaction notes

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