Acetic Acid → HCID 23062736, compound

HRID 1526861Notes

Reaction equation

HRID 1526861 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.[C:16](O)(=[O:18])[CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:16]([O:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:15])[CH2:4][CH2:3]1)(=[O:18])[CH3:17]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 516892Sodium BicarbonateHCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanol

Product 1

HCID 23062736HCID 23062736, compoundYield 21.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl N-(4-hydroxycyclohexyl)carbamate (15 g, 69.67 mmol, 1.00 equiv), acetic acid (16.7 g, 278.09 mmol, 4.00 equiv) and triphenylphosphane (73 g, 278.32 mmol, 4.00 equiv). In tetrahydrofuran (200 mL) was added diethyl azodicarboxylate (48.55 g, 278.78 mmol, 4.00 equiv) dropwise with stiffing at 0° C. The resulting solution was stirred overnight at room temperature and then 200 mL of aqueous sodium bicarbonate solution was added. The resulting mixture was extracted with 3×100 mL of ethyl acetate. The combined organic layers was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was triturated with 500 mL of a 1:1 mixture of ether and hexane. The solid triphenylphosphine oxide was removed by filtration. The filtrate was concentrated under vacuum and purified on a silica gel column eluted with ethyl acetate/petroleum ether (1:15) to give 3.8 g (21%) of 4-[[(tert-butoxy)carbonyl]amino]cyclohexyl acetate as a white solid.

Workup

  1. customwith stiffing at 0° C
  2. extractionThe resulting mixture was extracted with 3×100 mL of ethyl acetate
  3. dry with materialThe combined organic layers was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customThe crude product was triturated with 500 mL of a 1:1 mixture of ether and hexane
  6. customThe solid triphenylphosphine oxide was removed by filtration
  7. concentrationThe filtrate was concentrated under vacuum
  8. custompurified on a silica gel column
  9. washeluted with ethyl acetate/petroleum ether (1:15)

Sources & evidence

ORD record
ord-2af1af4b01224bb699fc170271264324
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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