Pyridine → HCID 131729156, compound

HRID 905953Notes

Reaction equation

HRID 905953 reaction equation
[C:1]([O:4][C:5](=O)[CH3:6])(=[O:3])[CH3:2].[C:8]([O:12][C:13](=[O:23])[NH:14][C@H:15]1[CH2:20]C[CH2:18][C@H:17](CO)[CH2:16]1)([CH3:11])([CH3:10])[CH3:9].N1C=CC=CC=1>C(Cl)Cl>[C:8]([O:12][C:13]([NH:14][C@H:15]1[CH2:16][CH2:17][CH2:18][C@H:6]([CH2:5][O:4][C:1](=[O:3])[CH3:2])[CH2:20]1)=[O:23])([CH3:11])([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 90307591rel-1,1-Dimethylethyl N-[(1R,3R)-3-(hydroxymethyl)cyclohexyl]carbamate

Product 1

HCID 131729156HCID 131729156, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Acetic anhydride (0.85 mL, 9.012 mmol) was added at 0° C. to a mixture of racemic trans 3-hydroxymethyl-cyclohexyl-carbamic acid tert-butyl ester (1.69 g, 7.37 mmol) and pyridine (0.78 mL, 9.646 mmol) in 20 mL of DCM. The resulting mixture was stirred at 0° C. to RT overnight and then at 50° C. for 4 hours before being cooled to RT and partitioned between DCM and aqueous 1M HCl. The aqueous layer was back extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated to give 2 g of racemic trans acetic acid 3-tert-butoxycarbonylamino-cyclohexylmethyl ester (>95% yield).

Workup

  1. custompartitioned between DCM and aqueous 1M HCl
  2. extractionThe aqueous layer was back extracted twice with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-141029b37ba542eca0ea1e0128fbd9f8
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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