Hydroxylamine → HCID 86682582, compound

HRID 2036211Notes

Reaction equation

HRID 2036211 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C@H:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]([O:32]CC)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:35][OH:36]>C(O)(C)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:20][CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[C@H:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30](=[O:32])[NH:35][OH:36])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 787HydroxylamineHCID 66654695HCID 66654695, compound

Product 1

HCID 86682582HCID 86682582, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To an ice-cooled solution of (S)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-3,4-dihydro-1H-isoquinoline-2-carboxylic acid benzyl ester (144 mg, 0.30 mmol, 1.0 eq.) in isopropanol (1.5 mL), hydroxylamine (50% w/w aqueous solution, 1.5 mL) was added. The ice bath was removed and the reaction mixture was stirred at r.t. for 18 hours. The reaction mixture was concentrated to half and water (5 mL) was added. The resulting suspension was filtered, washed with water and dried under hv to give the desired product as a white solid.

Workup

  1. additionwas added
  2. customThe ice bath was removed
  3. concentrationThe reaction mixture was concentrated to half and water (5 mL)
  4. additionwas added
  5. filtrationThe resulting suspension was filtered
  6. washwashed with water
  7. customdried under hv

Sources & evidence

ORD record
ord-a32e3c0bd7fb48eb8003cc089dae3ab5
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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