Sodium triacetoxyborohydride → HCID 56599194, compound

HRID 1035265Notes

Reaction equation

HRID 1035265 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][C:12]([C:14]([N:16]3[CH2:19][CH:18]([O:20][C:21]4[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=4)[CH2:17]3)=[O:15])=[N:11][N:10]=2)=[CH:5][CH:4]=1.[CH2:29]([C:31]1([CH2:37][OH:38])[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:29]([C:31]1([CH2:37][OH:38])[CH2:36][CH2:35][N:34]([CH2:25][C:24]2[CH:23]=[CH:22][C:21]([O:20][CH:18]3[CH2:19][N:16]([C:14]([C:12]4[O:13][C:9]([C:6]5[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=5)=[N:10][N:11]=4)=[O:15])[CH2:17]3)=[CH:28][CH:27]=2)[CH2:33][CH2:32]1)[CH3:30]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 510721784-Ethyl-4-piperidinemethanolHCID 580430894-(1-(5-(4-Methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde

Product 1

HCID 56599194HCID 56599194, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(1-(5-(4-methoxyphenyl)-1,3,4-oxadiazole-2-carbonyl)azetidin-3-yloxy)benzaldehyde (0.55 g, 1.45 mmol in DCM (30 mL) were added (4-ethylpiperidin-4-yl)methanol (0.27 g, 1.88 mmol, 1.3 equiv) and sodium triacetoxyborohydride (0.615 g, 2.90 mmol, 2 equiv). The reaction mixture was stirred at room temperature overnight and thereafter transferred to a reparatory funnel, washed with a saturated solution of Na2CO3, dried (phase separator) and concentrated under reduced pressure. The crude product was purified by automatic flash column chromatography using Biotage (eluting with EtOAc (10 CV), then EtOAc/MeOH (containing 2 M NH3) 20:1) on a 50 g snap column, collecting at UV 291 nm). The pure product fractions were combined and evaporated to afford the product as a white solid. Recrystallisation from DCM/Et2O afforded 280 mg, 38% of the product as a white solid (purity >99%). 1H NMR (400 MHz, CDCl3): δ 0.82 (t, 3H), 1.37-1.56 (m, 6H), 2.30-2.46 (m, 4H), 3.45 (2×s, 4H), 3.89 (s, 3H), 4.33 (dd, 1H), 4.64 (dd, 1H), 4.74 (dd, 1H), 5.03-5.15 (m, 2H), 6.72 (d, 2H), 7.02 (d, 2H), 7.25 (d, 2H), 8.1 (d, 2H), MS (APCI+) m/z 507 [M+H]+.

Workup

  1. customtransferred to a reparatory funnel
  2. washwashed with a saturated solution of Na2CO3
  3. customdried (phase separator)
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by automatic flash column chromatography
  6. washeluting with EtOAc (10 CV)
  7. customEtOAc/MeOH (containing 2 M NH3) 20:1) on a 50 g snap column, collecting at UV 291 nm)
  8. customevaporated

Sources & evidence

ORD record
ord-8beb8fc94e6a4dbbad13a386b3a57e5e
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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