Boron trifluoride etherate → 3-(2-Bromoethyl)-2-[(2-bromoethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one

HRID 1165302Notes

Reaction equation

HRID 1165302 reaction equation
[BH4-].[Na+].[Br:3][CH2:4][C:5]([N:7]1[CH2:12][CH2:11][CH2:10][O:9][P:8]1([NH:14][CH2:15][CH2:16][Br:17])=[O:13])=O.B(F)(F)F.CCOCC>O1CCCC1.C(Cl)(Cl)Cl.CC(C)=O.CO.O>[Br:3][CH2:4][CH2:5][N:7]1[CH2:12][CH2:11][CH2:10][O:9][P:8]1([NH:14][CH2:15][CH2:16][Br:17])=[O:13]

Participants

8

Reactant 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 14835219HCID 14835219, compound

Product 1

HCID 30731133-(2-Bromoethyl)-2-[(2-bromoethyl)amino]-1,3,2lambda~5~-oxazaphosphinan-2-one

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 15930782Chloroform acetoneSolvent

Procedure

Sodium borohydride (1.5 g) was added to the solution of 6.6 g (18.1 mM) of (+)-3-bromoacetyl-2[(2-bromoethyl)-amino]-2-oxo-1,3,2-oxazaphosphorinane {[α]D25 =+32.7° MeOH} in 45 mL of tetrahydrofuran at ambient temperature and then was added a solution of 5.2 mL of boron trifluoride etherate in 15 mL of tetrahydrofuran. The resulting suspension was stirred at room temperature until completed and then 15 mL of water was added. Following the isolation procedure described in Example II 5.7 g (90%) of the colorless crystalline product was obtained, mp. 93°-94.5° C.; 31P-NMR (CHCl3) δ 11.2 ppm(100%), [α]D25 =+37.86 (c 16 MeOH); TLC (CHCl3 -acetone 3:1) Rf 0.2; MS as in example II

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-9db59e58471b4516b01dd6b1db4da2e3
Source dataset
uspto-grants-1990_03
Patent number
US04908464

Reaction notes

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