Hydrochloric Acid → 1-benzyloctahydro-1H-pyrido[3,4-b][1,4]oxazine

HRID 81117Notes

Reaction equation

HRID 81117 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][C@@H:10]2[CH2:14][N:15](C(OC(C)(C)C)=O)[CH2:16][CH2:17][C@@H:9]12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CCOC(C)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]2[CH2:14][NH:15][CH2:16][CH2:17][CH:9]12)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90236606HCID 90236606, compound

Product 1

HCID 823902941-benzyloctahydro-1H-pyrido[3,4-b][1,4]oxazine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of trans-tert-butyl 1-benzyloctahydro-6H-pyrido[3,4-b][1,4]oxazine-6-carboxylate (82 g, 246 mmol) in EtOAc (500 mL) at 0° C. was added HCl in EtOAc (1500 mL, 4 M) dropwise. The reaction was stirred at room temperature for 2 hours. The mixture was concentrated to afford 1-benzyloctahydro-1H-pyrido[3,4-b][1,4]oxazine as a mixture of trans diastereomers.

Workup

  1. concentrationThe mixture was concentrated

Sources & evidence

ORD record
ord-508d3e33f6874c01ba6ef4778b8bb2b6
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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