(R)-beta-aminophenethyl alcohol → HCID 67080722, compound

HRID 655522Notes

Reaction equation

HRID 655522 reaction equation
C1C=CC([C@@H](N)CO)=CC=1.[C:11]([O:15][C:16](=[O:40])[N:17]([CH2:27][CH2:28][C:29](=[O:39])[NH:30]OCC1C=CC=CC=1)[C@H:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:19]O)([CH3:14])([CH3:13])[CH3:12].C(OC(N1CCC(=O)N(OCC2C=CC=CC=2)C[C@H]1C1C=CC=CC=1)=O)(C)(C)C>>[C:11]([O:15][C:16]([N:17]1[CH2:27][CH2:28][C:29](=[O:39])[NH:30][CH2:19][C@H:18]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:40])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 2724025(R)-beta-aminophenethyl alcoholHCID 67080695HCID 67080695, compoundHCID 86638109HCID 86638109, compound

Product 1

HCID 67080722HCID 67080722, compound

Procedure

The title compound, m/e=416.4, was produced in analogy with intermediate 16, steps A to D. Thus, D-phenylglycinol was elaborated to (2-benzyloxycarbamoyl-ethyl)-((R)-2-hydroxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester in step A, then cyclized in step B, leading to (R)-4-benzyloxy-5-oxo-2-phenyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester. Hydrogenation in step C gave (R)-5-oxo-2-phenyl-[1,4]diazepane-1-carboxylic acid tert-butyl ester, which was alkylated with 1-(3-chloropropyl)piperidine in step D.

Sources & evidence

ORD record
ord-1667684161844015abbf9a5582b19110
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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