Acetic Acid → HCID 86596967, compound

HRID 2225289Notes

Reaction equation

HRID 2225289 reaction equation
C(O)(=O)C.O.[Si]([O:13][CH2:14][C@@H:15]1[CH2:20][C:19](=[O:21])[CH2:18][CH2:17][C@@H:16]1[NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:13][CH2:14][C@@H:15]1[CH2:20][C:19](=[O:21])[CH2:18][CH2:17][C@@H:16]1[NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 86596966HCID 86596966, compound

Product 1

HCID 86596967HCID 86596967, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of acetic acid, water, and THF (30 mL, 3:1:1) was added to benzyl (1S,2R)-2-((tert-butyldimethylsilyloxy)methyl)-4-oxocyclohexylcarbamate (2.56 g) in one portion. After 48 h, the reaction solvent was removed in vacuo and replaced with ethyl acetate (100 mL). The mixture was washed with water (1×25 mL), sat'd NaHCO3 (2×25 mL), and brine (1×25 mL). The resulting organic layer was dried over MgSO4, filtered, and then evaporated to dryness in vacuo to give benzyl (1S,2R)-2-(hydroxymethyl)-4-oxocyclohexylcarbamate (1.80 g) as a clear viscous oil after drying under vacuum overnight: 1H NMR (300 MHz, CDCl3) δ 7.37 (s, 5H), 5.57 (d, J=6.9 Hz, 1H), 5.13 (s, 2H), 4.25 (br s, 1H), 3.69 (m, H), 3.45 (m, 2H), 2.38-2.02 (m, 7H).

Workup

  1. customthe reaction solvent was removed in vacuo
  2. washThe mixture was washed with water (1×25 mL), sat'd NaHCO3 (2×25 mL), and brine (1×25 mL)
  3. dry with materialThe resulting organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-ca3729e9450047aa8ea9e4f7c8579b1d
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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