Lithium borohydride → HCID 89815531, compound

HRID 1487142Notes

Reaction equation

HRID 1487142 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][CH:20]=1)[C:7]([NH:9][C:10]1([C:13](OCC)=[O:14])[CH2:12][CH2:11]1)=[O:8])([O-:3])=[O:2].[Li+].[BH4-]>O1CCCC1>[OH:14][CH2:13][C:10]1([NH:9][C:7](=[O:8])[C:6]2[CH:18]=[CH:19][CH:20]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 89815426HCID 89815426, compound

Product 1

HCID 89815531HCID 89815531, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
45 °C

Procedure

To the suspension of ethyl 1-(3-nitrobenzamido)cyclopropanecarboxylate (0.400 g, 1.438 mmol) in tetrahydrofuran 10 ml, LiBH4 (0.063 g, 2.88 mmol) was added and heated the content at 45° C. for 15 hr. Reaction mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate (2×10 ml). Organic layer was dried over sodium sulfate and concentrated under vacuum which was further purified by column chromatography eluting ethyl acetate (0-70%) in hexane (0.05 g, 14%).

Workup

  1. additionwas added
  2. customReaction mixture
  3. customwas quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate (2×10 ml)
  5. dry with materialOrganic layer was dried over sodium sulfate
  6. concentrationconcentrated under vacuum which
  7. customwas further purified by column chromatography
  8. washeluting ethyl acetate (0-70%) in hexane (0.05 g, 14%)

Sources & evidence

ORD record
ord-a3477037ae49459c884a014653e8b5d6
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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