Boron tribromide → Ammonia

HRID 450939Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([O:35]C)[CH:34]=1)[O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([CH3:31])([CH3:30])[CH2:12][CH2:13][C:14]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([NH2:17])=[O:16])[CH2:7]1.B(Br)(Br)Br>>[F:1][C:2]1[CH:3]=[C:4]([CH:32]=[C:33]([OH:35])[CH:34]=1)[O:5][C@H:6]1[CH2:10][CH2:9][N:8]([C:11]([CH3:30])([CH3:31])[CH2:12][CH2:13][C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:15]([NH2:17])=[O:16])[CH2:7]1.[NH3:8]

Participants

Reactant 2

HCID 25134Boron tribromide

HCID 59423961HCID 59423961, compound

Product 2

HCID 222Ammonia

HCID 16065264HCID 16065264, compound

Procedure

The title compound was prepared from the product of example 45, using the same method as that described for example 34, with the addition of further boron tribromide (1M in dichloromethane, 4 eq) after 3 hours, and subsequent stirring for 2 hrs. Crude material was purified by column chromatography on silica gel, eluting with ethyl acetate:methanol:0.88 ammonia, 98:2:0.2 to 94:6:0.6 to afford a white foam in 35% yield.

Workup

customCrude material was purified by column chromatography on silica gel
washeluting with ethyl acetate

Sources & evidence

ORD record: ord-280cda24e00b4f11bd427bfd7ac902da
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486992B2

Reaction notes

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