Hydroxylamine → HCID 59271841, compound

HRID 1893188Notes

Reaction equation

HRID 1893188 reaction equation
[C:1]([CH:3]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:4][CH2:5][C:6]([CH3:16])([CH3:15])[CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)#[N:2].[NH2:26][OH:27]>CO>[NH2:2]/[C:1](=[N:26]\[OH:27])/[CH:3]([N:17]([CH3:25])[C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:4][CH2:5][C:6]([CH3:16])([CH3:15])[CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 59271850HCID 59271850, compound

Product 1

HCID 59271841HCID 59271841, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of tert-butyl [1-cyano-4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentyl]methylcarbamate (8.5 g, 23.98 mmol), in methanol (5 mL) was added 50% hydroxylamine (1.543 mL, 25.2 mmol). The mixture was heated to 60° C. for 3 hours (LC-MS indicates complete conversion) cooled and concentrated. Removal of excess hydroxylamine azeotropically with methanol gave tert-butyl [1-[(Z)-amino(hydroxyimino)methyl]-4,4-dimethyl-5-(tetrahydro-2H-pyran-2-yloxy)pentyl]methylcarbamate: MS (ES+): 388.26 (M+H).

Workup

  1. temperaturecooled
  2. concentrationconcentrated
  3. customRemoval of excess hydroxylamine azeotropically with methanol

Sources & evidence

ORD record
ord-7e0d5ddbe1114ded93b5691d8d9685b9
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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