HCID 54406880, compound → HCID 53706962, compound

HRID 617759Notes

Reaction equation

HRID 617759 reaction equation
[C:1]([N:11]([C@@H:13]([CH3:23])[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)[CH3:12])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]>C(O)C.Cl>[C:1]([N:11]([C@@H:13]([CH3:23])[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1)[CH3:12])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 1

HCID 54406880HCID 54406880, compound

Product 1

HCID 53706962HCID 53706962, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

α-A solution of (S)-(-)-N-carbobenzyloxy-N-methyl-methyl-4-nitrobenzylamine (6.6 gm, 21 imol) in 100% ethanol (100 mL) was cooled in an ice bath while a solution of stannous chloride dihydrate (14.2 gm, 63 mmol) in conc. hydrochloric acid (25 mL) was added. The reaction was allowed to warm to rt over 14 hrs and was then quenched into a solution of ice, 5N sodium hydroxide (100 mL) and ether and the pH adjusted to 9-10. The layers were separated and the ether layer was washed with brine. The aqueous layers were consecutively extracted with a second portion of ether and the pooled ether layers were dried over sodium sulfate and evaporated. The residue was partially purified by flash chromatography using 20-30% ethyl acetate/hexanes, then 5% methanol/30% ethyl acetate/65% hexanes to give 6.0 gm of impure title compound containing variable amounts of benzyloxycarbonylmethylamine.

Workup

  1. additionwas added
  2. customwas then quenched into a solution of ice, 5N sodium hydroxide (100 mL) and ether
  3. customThe layers were separated
  4. washthe ether layer was washed with brine
  5. extractionThe aqueous layers were consecutively extracted with a second portion of ether
  6. dry with materialthe pooled ether layers were dried over sodium sulfate
  7. customevaporated
  8. customThe residue was partially purified by flash chromatography

Sources & evidence

ORD record
ord-84e671bd24194946947c468ed157720c
Source dataset
uspto-grants-1999_09
Patent number
US05952321

Reaction notes

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