Ethanol → (-)-(cis)-7-bromo-8,11-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 1668365Notes

Reaction equation

HRID 1668365 reaction equation
[Br:1][C:2]1[C:22]([F:23])=[CH:21][C:5]2[O:6][C:7]3[C:19]([F:20])=[CH:18][CH:17]=[CH:16][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.[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(O)C>C(Cl)Cl>[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[C:19]([F:20])=[CH:18][CH:17]=[CH:16][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

5

Reactant 3

HCID 702EthanolHCID 9829482(4R)-2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan 2-oxideHCID 67358065(+/-)-(cis)-7-Bromo-8,11-difluoro-1,3,4,14b-tetrahydro-2h-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine

Product 1

HCID 67358064(-)-(cis)-7-bromo-8,11-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 26.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation analogous to Example 5, step i, from (±)-(cis)-7-bromo-8,11-difluoro-1,3,4,14b-tetrahydro-2H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepine-1-amine (30.5 mmol) and (+)-phencyphos (3.7 g, 15.29 mmol) in CH2Cl2 (160 mL), and ethanol (100 mL). Recrystallization gave the title compound (2.55 g, 17%).

Workup

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

Sources & evidence

ORD record
ord-ae9ea876c64b4b1da32a6fcb172605c0
Source dataset
uspto-grants-2011_08
Patent number
US07989442B2

Reaction notes

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