Morpholine → HCID 69695131, compound

HRID 489917Notes

Reaction equation

HRID 489917 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([OH:10])=[O:9])[CH2:3]1.C(OP(ON1C(=O)C2C=CC=CC=2N=N1)(OCC)=O)C.C(N(CC)C(C)C)(C)C.[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>ClCCl>[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([OH:10])=[O:9])[CH2:3]1.[N:40]1([C:8]([C@@H:4]2[CH2:5][CH2:6][CH2:7][C:2](=[O:1])[CH2:3]2)=[O:10])[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 12924365(1R)-3-Oxocyclohexane-1-carboxylic acid

Product 2

HCID 12924365(1R)-3-Oxocyclohexane-1-carboxylic acidHCID 69695131HCID 69695131, compoundYield 107.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(1R)-3-Oxo-cyclohexanecarboxylic acid was prepared according to the procedure described by R. D. Allan et al. in Aust. J. Chem., 1981, 34, 2231. A solution of (1R)-3-oxo-cyclohexanecarboxylic acid (1 eq, 2.52 g, 18.1 mmol), 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT, H. Li et al. Organic Letters, 1999, 1, 91) (1.05 eq, 19.0 mmol, 5.68 g) and N,N-diisopropylethylamine (15 eq, 27.1 mmol, 4.7 mL) in anhydrous dichloromethane (70 mL) was allowed to stir at room temperature for 75 minutes. Morpholine (1.2 eq, 21.72 mmol, 1.9 mL) was added and the solution was stirred at ambient temperature for 16 h. The mixture was concentrated under vacuum to an oil which was purified by flash chromatography eluting with a 2.5% methanol-dichloromethane gradient on silica gel to give (3R)-3-(morpholine-4-carbonyl)-cyclohexanone (2.05 g, 54%).

Workup

  1. stirringthe solution was stirred at ambient temperature for 16 h
  2. concentrationThe mixture was concentrated under vacuum to an oil which
  3. customwas purified by flash chromatography
  4. washeluting with a 2.5% methanol-dichloromethane gradient on silica gel

Sources & evidence

ORD record
ord-eb5ca70d0e46438c94bd19f5f449eb6d
Source dataset
uspto-grants-2005_12
Patent number
US06979741B2

Reaction notes

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