Sodium Hydroxide → 8-{2-[(S)-1-(4-bromo-phenyl)-ethylamino]-ethyl}-1,4-dioxa-spiro[4.5]decan-8-ol

HRID 1615114Notes

Reaction equation

HRID 1615114 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH:25][C:26]1([CH2:36][CH:37]=O)[CH2:35][CH2:34][C:29]2([O:33][CH2:32][CH2:31][O:30]2)[CH2:28][CH2:27]1.[OH-].[Na+]>O1CCCC1.O.C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:37][CH2:36][C:26]2([OH:25])[CH2:35][CH2:34][C:29]3([O:30][CH2:31][CH2:32][O:33]3)[CH2:28][CH2:27]2)[CH3:9])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 57815370(8-Hydroxy-1,4-dioxa-spiro[4.5]dec-8-yl)-acetaldehyde

Product 1

HCID 679963538-{2-[(S)-1-(4-bromo-phenyl)-ethylamino]-ethyl}-1,4-dioxa-spiro[4.5]decan-8-ol

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(S)-1-(4-Bromo-phenyl)-ethylamine (2.68 g), sodium triacetoxyborohydride (2.84 g), and acetic acid (0.77 mL) are added in the given order to a solution of (8-hydroxy-1,4-dioxa-spiro[4.5]dec-8-yl)-acetaldehyde (7.86 g) in tetrahydrofuran (150 mL) at room temperature. The resulting mixture is stirred at room temperature overnight. Water (100 mL) and 1 M aqueous NaOH solution (100 mL) are then added and the mixture is stirred for another 20 min. The mixture is extracted with ethyl acetate, and the combined extracts are washed with water and brine. After drying (MgSO4), the solvent is evaporated to give the crude title compound that is used without further purification. Yield: 2.91 g (crude); LC (method 3): tR=2.00 min; Mass spectrum (ESI+): m/z=384/386 (Br) [M+H]+.

Workup

  1. stirringthe mixture is stirred for another 20 min
  2. extractionThe mixture is extracted with ethyl acetate
  3. washthe combined extracts are washed with water and brine
  4. dry with materialAfter drying (MgSO4)
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-1aaeb7491ffb4d73a5f34b0eb1c758ab
Source dataset
uspto-grants-2014_07
Patent number
US08765744B2

Reaction notes

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