Propanal → HCID 11362947, compound

HRID 393206Notes

Reaction equation

HRID 393206 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][C:19]([Br:25])=[CH:20][CH:21]=3)[CH2:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:26](=O)[CH2:27][CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH:15]2[CH2:24][CH2:23][C:22]3[C:17](=[CH:18][C:19]([Br:25])=[CH:20][CH:21]=3)[CH2:16]2)[CH2:26][CH2:27][CH3:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 114412094-(7-Bromo-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 11362947HCID 11362947, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 4-(7-bromo-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester (610 mg, 1.5 mmol) and propionaldehyde (0.1 mL, 1.5 mmol) in dichloroethane (20 mL) under a nitrogen atmosphere was added sodium triacetoxyborohydride (795 mg, 3.75 mmol) in a single portion. The reaction was stirred at room temperature for 24 h then concentrated in vacuo. The residue was partitioned between EtOAc (75 mL) and 5% aq. KOH (50 mL). The aqueous phase was extracted twice more with EtOAc (2×30 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated onto silica (10 g). This was placed on top of a flash column and eluted with 20% hexanes in acetone. The fractions containing product were pooled and concentrated to afford 4-[(7-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-propyl-amino]-piperidine-1-carboxylic acid tert-butyl ester (587 mg).

Workup

  1. concentrationthen concentrated in vacuo
  2. customThe residue was partitioned between EtOAc (75 mL) and 5% aq. KOH (50 mL)
  3. extractionThe aqueous phase was extracted twice more with EtOAc (2×30 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated onto silica (10 g)
  7. washeluted with 20% hexanes in acetone
  8. additionThe fractions containing product
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d0f72e9ca1564a249793e453102ad14c
Source dataset
uspto-grants-2004_10
Patent number
US06806278B2

Reaction notes

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