Aluminium lithium hydride → tert-Butyl (2S,4R)-4-(6-aminopyridin-3-yl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 595828Notes

Reaction equation

HRID 595828 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:10]([C:20](OC)=[O:21])[CH2:9]2)=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C@@H:8]2[CH2:12][N:11]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[C@H:10]([CH2:20][OH:21])[CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 1180462431-(tert-Butyl) 2-methyl (2S,4R)-4-(6-aminopyridin-3-yl)pyrrolidine-1,2-dicarboxylate

Product 1

HCID 118045668tert-Butyl (2S,4R)-4-(6-aminopyridin-3-yl)-2-(hydroxymethyl)pyrrolidine-1-carboxylateYield 100.8%

Procedure

To a solution of (2S,4R)-1-tert-butyl 2-methyl 4-(6-aminopyridin-3-yl)pyrrolidine-1,2-dicarboxylate (250 mg, 0.778 mmol) in 2-methyl THF (18 mL) was added LiAlH4 (59 mg, 1.56 mmol). After 15 min, the reaction was quenched by the sequential addition of water (60 μL), 1 N NaOH aqueous solution (60 μL) and water (60 μL). The mixture was stirred vigorously for 5 min, and then filtered over Celite, rinsing with 2-methyl THF. The organics were concentrated to provide (2S,4R)-tert-butyl 4-(6-aminopyridin-3-yl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate (230 mg, 100% yield). LCMS (m/z): 294.1 (MH+), 0.49 min.

Workup

  1. customthe reaction was quenched by the sequential addition of water (60 μL), 1 N NaOH aqueous solution (60 μL) and water (60 μL)
  2. filtrationfiltered over Celite
  3. washrinsing with 2-methyl THF
  4. concentrationThe organics were concentrated

Sources & evidence

ORD record
ord-9f34ef52ec6448cba10c0b39075881be
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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