Sodium borohydride → (R)-2-[4-(2-fluorobenzyloxy)benzylamino]propanamide

HRID 83471Notes

Reaction equation

[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:18]=[CH:17][C:9]([CH:10]=[N:11][C@H:12]([CH3:16])[C:13]([NH2:15])=[O:14])=[CH:8][CH:7]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[CH:19][C:3]=1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([CH2:10][NH:11][C@H:12]([CH3:16])[C:13]([NH2:15])=[O:14])=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 3.5 °C

Procedure

A mixture of (R)-2-[4-(2-fluorobenzyloxy)benzylideneamino]propanamide (III′b) (30 g) and of methanol (180 mL) is cooled under stirring to 2-5° C. Sodium borohydride (3.8 g) is added in twenty small portions in 90 min to the previously prepared cold mixture keeping the temperature below 5° C. The mixture is then stirred for additional 10 min at 5° C. The reaction mixture is concentrated under vacuum and worked up as described in Example 2 to provide 28.44 g (94% yield of (R)-2-[4-(2-fluorobenzyloxy)benzylamino]propanamide (I′b) with a HPLC purity of 99.8 (area %) determined according to the method of Example 25A and a C,O-dialkylated (R)-2-[3-(2-fluorobenzyl)-4-(2-fluorobenzyloxy)-benzylamino]propanamide content less than 0.005% by weight determined by HPLC, according to the method of Example 25B.

Workup

customthe temperature below 5° C
stirringThe mixture is then stirred for additional 10 min at 5° C
concentrationThe reaction mixture is concentrated under vacuum

Sources & evidence

ORD record: ord-6b75a3dc1f014d24b5e4ea66ea3b7eb0
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846763B2

Reaction notes

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