Sodium borohydride → 1-amino-3-[3-(benzyloxy)phenyl]-5-(hydroxymethyl)-1H-pyrrole-2-carbonitrile

HRID 1972811Notes

Reaction equation

[NH2:1][N:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:10]=2)[CH:4]=[C:3]1[C:23](OCC)=[O:24].[BH4-].[Na+]>C(O)C>[NH2:1][N:2]1[C:3]([CH2:23][OH:24])=[CH:4][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:10]=2)=[C:6]1[C:7]#[N:8]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 1-amino-4-[3-(benzyloxy)phenyl]-5-cyano-1H-pyrrole-2-carboxylate (1.00 g, 2.77 mmol) in ethanol (24 mL) was added sodium borohydride (523 mg, 13.8 mmol). The mixture was heated (80° C.) for 17 h and then cooled to rt. The reaction was quenched with the addition of water (25 mL) and the mixture was extracted with ethyl acetate (2×25 mL). The combined organics were washed with brine, dried (Na2SO4) and concentrated to dryness to obtain 883 mg (100%) of the desired product. 1H NMR (300 MHz, DMSO-d6) δ 7.48-7.42 (m, 2 H), 7.41-7.28 (m, 4 H), 7.25-7.19 (m, 2 H), 6.97-6.93 (m, 1 H), 6.41 (s, 1 H), 6.07 (s, 2 H), 5.23 (t, 1 H), 5.13 (s, 2 H), 4.49 (d, 2 H).

Workup

temperaturecooled to rt
customThe reaction was quenched with the addition of water (25 mL)
extractionthe mixture was extracted with ethyl acetate (2×25 mL)
washThe combined organics were washed with brine
dry with materialdried (Na2SO4)
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-9b092813ba7a4f0f8f91dc199de455d4
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431695B2

Reaction notes

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