Dimethylformamide → HCID 68751819, compound

HRID 1038836Notes

Reaction equation

HRID 1038836 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][C@H:4]1[OH:16].CN([CH:20]=[O:21])C.C1N=CN(C(N2C=NC=C2)=O)C=1>CCOC(C)=O>[CH2:9]([N:6]1[CH2:7][CH2:8][C@H:3]2[CH2:2][NH:1][C:20](=[O:21])[O:16][C@@H:4]2[CH2:5]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 682631,1'-CarbonyldiimidazoleHCID 57986572rel-(3R,4R)-4-(Aminomethyl)-1-(phenylmethyl)-3-piperidinol

Product 1

HCID 68751819HCID 68751819, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

In a flask, was added (3S,4S)-4-(aminomethyl)-1-benzylpiperidin-3-ol (1.0 g, 4.5 mmol, Sunshine Labs), DMF (10 mL) and CDI (0.736 g, 4.54 mmol). The mixture was heated to about 65° C. for about 40 min. To the mixture was added EtOAc (20 mL) and washed with water (3×20 mL). The aqueous layers were combined and extracted with DCM (2×20 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under vacuum to give (4aS,8aS)-7-benzyloctahydro-2H-pyrido[4,3-e][1,3]oxazin-2-one (0.773 g, 69%): LC/MS (Table 2, Method c) Rt=1.11 min.; MS m/z: 247 (M+H)+.

Workup

  1. washwashed with water (3×20 mL)
  2. extractionextracted with DCM (2×20 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c46d4a200ee840988354d45862bd1c8f
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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