tert-Butyl methyl ether → HCID 11151078, compound

HRID 541062Notes

Reaction equation

HRID 541062 reaction equation
[CH:1]([CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:2].[BH4-].[Na+].C(NC1C=CC2C3C(=CC=CC=3)CC=2C=1)(OC(C)(C)C)=O.CC(OC)(C)C>CO.O.CCOC(C)=O.CC(O)=O>[OH:2][CH2:1][CH:3]1[C:15]2[CH:14]=[C:13]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2

Participants

9

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 4311764Sodium borohydrideHCID 113120632-(Boc-amino)fluoreneHCID 11347396HCID 11347396, compound

Product 1

HCID 11151078HCID 11151078, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

9-Formyl-2-(Boc-amino)fluorene was suspended in 100 ml methanol and 2.0 g NaBH4 [52.9 mmol, 1.1 equiv with respect to the starting 2-(Boc-amino)fluorene] was added portion wise. The suspension that rapidly cleared up was magnetically stirred until the starting product disappeared for 4 h at room temperature [TLC, Rf=0.57, PE:MTBE (1:2)]. The reaction mixture was diluted with 300 ml H2O and acidified with 15 ml glacial HOAc to pH 5.0, and the precipitate was directly dissolved in 150 ml EtOAc. The organic phase was washed with 3×50 ml sat. NaHCO3 and 1×50 ml brine and dried over anhydrous Na2SO4. The solvent was rotary evaporated to give a solid, which could be used without further purification. The product was analyzed by NMR (13.1 g, 88% yield).

Workup

  1. washThe organic phase was washed with 3×50 ml sat. NaHCO3 and 1×50 ml brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was rotary evaporated
  4. customto give a solid, which
  5. customcould be used without further purification

Sources & evidence

ORD record
ord-8693e7a9f034413699b32c934df96c9f
Source dataset
uspto-grants-2014_10
Patent number
US08871949B2

Reaction notes

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