Acetic Acid → HCID 68932625, compound

HRID 32120Notes

Reaction equation

HRID 32120 reaction equation
[C:1]([O:5][C:6](=[O:21])[N:7]([CH:9]1[C:18]2[C:13](=[CH:14][C:15]([CH:19]=O)=[CH:16][CH:17]=2)[O:12][CH2:11][CH2:10]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[NH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC(O)=O>ClCCCl>[C:1]([O:5][C:6](=[O:21])[N:7]([CH3:8])[CH:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][N:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)=[CH:16][CH:17]=2)[O:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 58841404HCID 58841404, compound

Product 1

HCID 68932625HCID 68932625, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of (7-formyl-chroman-4-yl)-methyl-carbamic acid tert-butyl ester (554 mg, 1.90 mmol, 1.0 eq), piperidine (Aldrich, 195 mg, 2.28 mmol, 1.2 eq), NaBH(OAc)3 (Aldrich, 805 mg, 3.8 mmol, 2.0 eq) and glacial HOAc (J. T. Baker, 114 mg, 1.90 mmol, 1.0 eq) in ClCH2—CH2Cl (8 mL) was stirred at RT for 4 h. The reaction was quenched with saturated Na2CO3 (50 mL) The crude was extracted with CH2Cl2 (60 mL×3). The extract phase was washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. Flash column chromatography (silica gel, 0-5% MeOH—CH2Cl2) afforded the title compound as colorless sticky solid. MS (ESI, pos. ion) m/z: 361 (M+1).

Workup

  1. customThe reaction was quenched with saturated Na2CO3 (50 mL) The crude
  2. extractionwas extracted with CH2Cl2 (60 mL×3)
  3. washThe extract phase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-673af49992a84b08ad2b2e5893e5a885
Source dataset
uspto-grants-2008_09
Patent number
US07425631B2

Reaction notes

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