Hydroxylamine → HCID 18316227, compound

HRID 276254Notes

Reaction equation

HRID 276254 reaction equation
[NH2:1][C:2]1([C:9]([OH:11])=O)[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][CH2:5]2.N[C:13]1([CH2:20]O)[CH2:18]C2C[CH:14]1CC2.NO.C(Br)C(C)C>CN(C=O)C>[CH2:14]([NH:1][C:2]1([CH2:9][OH:11])[CH2:7][CH:6]2[CH2:8][CH:3]1[CH2:4][CH2:5]2)[CH:13]([CH3:20])[CH3:18]

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 65551-Bromo-2-methylpropaneHCID 1152882-Aminonorbornane-2-carboxylic acidHCID 18315959HCID 18315959, compound

Product 1

HCID 18316227HCID 18316227, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Aminonorbornane-2-carboxylic acid was converted into 2-amino-2-(hydroxymethyl)norbornane as a diastereomeric mixture in a manner analogous to Method B1a. A solution of the amino alcohol (0.31 g, 2.16 mmol) and isobutyl bromide (0.23 ml, 2.16 ml) in DMF (3 mL) was heated at 90° C. for 92 h, then cooled to room temp. and partitioned between EtOAc (100 mL) and a saturated NaHCO3 solution (100 mL). The organic layer was washed with a saturated NaCl solution (50 mL), dried (MgSO4), and concentrated under reduced pressure to yield 2-(isobutylamino)-2-(hydroxymethyl)norbornane as a diastereomeric mixture (0.24 g, 55%): GC-MS m/z 197 (M+).

Workup

  1. temperaturecooled to room temp.
  2. custompartitioned between EtOAc (100 mL)
  3. washThe organic layer was washed with a saturated NaCl solution (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5665a6c847e74a678f1d1fd2c8413c97
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

Loading…