Water → (3RS,4R)-4-(Trityl-amino)-hexan-3-ol

HRID 1432397Notes

Reaction equation

HRID 1432397 reaction equation
[C:1]([NH:20][C@H:21]([CH2:24][CH3:25])[CH:22]=[O:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:26]([Mg]Br)[CH3:27].O>CCOCC>[C:1]([NH:20][C@H:21]([CH2:24][CH3:25])[CH:22]([OH:23])[CH2:26][CH3:27])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 57714153(R)-2-(Trityl-amino)-butyraldehydeHCID 178418443HCID 178418443, compound

Product 1

HCID 57714154(3RS,4R)-4-(Trityl-amino)-hexan-3-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of (R)-2-(trityl-amino)-butyraldehyde (1.5 g, 1 eq, 4.53 mmol) in ether (150 mL) under an argon atmosphere at −78° C., was added ethylmagnesium bromide (3 M in ether, 1.51 mL, 1 eq, 4.53 mmol) dropwise. The solution was sired at −78° C. for 2 h, then allowed to warm to room temperature over 16 h. The mixture was re-cooled to 0° C., H2O (150 mL) added, and the organic phase separated. The aqueous phase was extracted with more ether (2×50 mL), and the combined organic phase washed with brine (50 mL), dried (MgSO4) and evaporated in vacuo. The residue was purified by silica gel column chromatography, eluted with hexane:ether (90:10) to afford the title compound as a light yellow oil; Yield: 1.13 g (69%): (57% A de 3S,4R: 43% de 3R,4R). 1H-NMR (d6-DMSO, 250 MHz): δ 0.45+0.69 (t+m, 6H, J=7.43 Hz, —NHCH(CH2CH3)CH(CH2CH3)OH), 1.12-1.29 (m, 4H, —NHCH(CH2CH3)CH(CH2CH3)OH), 2.16 (m, 1H, —NHCH(CH2CH3)CH(CH2CH3)OH), 2.54 (m, 1H, —NHCH(CH2CH3)CH(CH2CH3)OH), 3.21-3.40 (m, 1H, —NHCH(CH2CH3)CH(CH2CH3)OH), 4.29+4.39 (2×d, 1H, J=4.42+5.37 Hz, —NHCH(CH2CH3)CH(CH2CH3)OH), 7.15-7.52 (m, 15H, 3×Bz).

Workup

  1. temperatureThe mixture was re-cooled to 0° C.
  2. customthe organic phase separated
  3. extractionThe aqueous phase was extracted with more ether (2×50 mL)
  4. washthe combined organic phase washed with brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluted with hexane:ether (90:10)

Sources & evidence

ORD record
ord-d0f801128dfb48acb41cbc712ba966dd
Source dataset
uspto-grants-2009_11
Patent number
US07612079B2

Reaction notes

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