Ethanol → (-)-(cis)-7-bromo-8,14-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (4S)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxide

HRID 1668362Notes

Reaction equation

HRID 1668362 reaction equation
[Br:1][C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][C:7]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:8]=3[CH:9]3[CH:14]([NH2:15])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1.[CH3:24][C:25]1([CH3:39])[C@@H:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[O:30][P:28]([OH:38])(=[O:29])[O:27][CH2:26]1.C(Cl)Cl.C(O)C>CC(=O)CC>[OH:38][P:28]1(=[O:29])[O:30][C@@H:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:25]([CH3:24])([CH3:39])[CH2:26][O:27]1.[Br:1][C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][C:7]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[C:8]=3[C@H:9]3[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][N:10]3[C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6344DichloromethaneHCID 9829482(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxideHCID 673586397-bromo-8,14-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

Product 1

HCID 67360816(-)-(cis)-7-bromo-8,14-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (4S)-2-hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinane 2-oxideYield 27%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

Preparation analogous to Example 5, step i, from 2.2 g, (5.77 mmol) of (±)-(cis)-(7-bromo-8,14-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine, 0.7 g, (2.88 mmol) of (+)-phencyphos, CH2Cl2 (100 mL), ethanol (5 mL) and 2-butanone (50 mL). Recrystallization gave the title compound (0.8 g, 27%).

Workup

  1. customPreparation analogous to Example 5, step i
  2. customRecrystallization

Sources & evidence

ORD record
ord-ff51b3cfd01d4802af0f3801c8435720
Source dataset
uspto-grants-2011_08
Patent number
US07989442B2

Reaction notes

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