Water → HCID 67437669, compound

HRID 1968897Notes

Reaction equation

HRID 1968897 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]([CH:13]=O)[C@@H:9]([CH3:12])[CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:18]=[C:19]2[C:24](=[CH:25][CH:26]=1)[CH:23]=[C:22]([NH2:27])[CH:21]=[CH:20]2.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>ClCCCl>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]([CH2:13][NH:27][C:22]1[CH:21]=[CH:20][C:19]2[C:24](=[CH:25][CH:26]=[C:17]([Br:16])[CH:18]=2)[CH:23]=1)[C@@H:9]([CH3:12])[CH2:10][CH3:11])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3484042-Amino-6-bromonaphthaleneHCID 5049666Sodium triacetoxyborohydrideHCID 113902721,1-Dimethylethyl N-((1S,2S)-1-formyl-2-methylbutyl)carbamate

Product 1

HCID 67437669HCID 67437669, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

((1S,2S)-1-Formyl-2-methyl-butyl)-carbamic acid tert-butyl ester (1.62 g, 7.5 mmol), and 6-bromo-naphthalen-2-ylamine (1.11 g, 5.0 mmol) were combined in DCE (10 mL). After stirring 5 min, NaBH(OAc)3 (2.33 g, 11 mmol) was added. The whole mixture was then stirred at r.t. for 18 h. The reaction mixture was transferred to a separatory funnel containing water (50 mL). The aqueous layer was extracted with DCM (3×50 mL). The combined organic layers were washed with brine (50 mL), dried over MgSO4, filtered and concentrated. The residue was purified via column chromatography on silica gel (10% ethyl acetate in hexanes) to afford {(1S,2S)-1-[(6-bromo-naphthalen-2-ylamino)-methyl]-2-methyl-butyl}-carbamic acid tert-butyl ester (1.78 g, 85% yield) as an off-white solid. LC/MS (ESI) m/e 423.2 [(M+H)+, calcd for C21H29BrN2O2 421.4].

Workup

  1. stirringThe whole mixture was then stirred at r.t. for 18 h
  2. customThe reaction mixture was transferred to a separatory funnel
  3. extractionThe aqueous layer was extracted with DCM (3×50 mL)
  4. washThe combined organic layers were washed with brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified via column chromatography on silica gel (10% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e4c33d908688424daf4bae7416a3ffa3
Source dataset
uspto-grants-2013_04
Patent number
US08426414B2

Reaction notes

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